Covalent binding of PCB metabolites to lipids: route of formation and characterization

References

• AMARO, A. R., OAKLEY, G. G., BAUER, U., SPIELMANN, H.-P. and ROBERTSSON, L. W., 1996, Metabolic activation of PCBs to quinones: reactivity toward nitrogen and sulfur nucleophiles and influence of superoxide dismutase. Chemical Research in Toxicology, 9, 623–629.
   Google Scholar
• ANSARI, G. A. S., BRITT, S. G. and REYNOLDS, E. S., 1985, Isolation and characterisation of palmitoyl-pentachlorophenol from human fat. Bulletin of Environmental Contamination and Toxicology, 34, 661–667.
   Google Scholar
• ANSARI, G. A. S., KAPHALIA, B. S. and KHAN, M. F., 1995, Mini Review. Fatty acid conjugates of xenobiotics. Toxicology Letters, 75, 1–17.
   Google Scholar
• BAKKE, J., FEIL, V. and BERGMAN, A., 1983, Metabolites of 2,4',5-trichlorobiphenyl in rats. Xenobiotica, 13, 555–564.
   PubMed Web of Science ®Google Scholar
• BAKKE, J. and GUSTAVSSON, J.-À., 1986, Role of the intestinal microflora in metabolism of polychlorinated biphenyls. In B. Hallgren et al. (eds), Diet and Prevention of Coronary Heart Disease and Cancer (New York: Raven), pp. 47–54.
   Google Scholar
• BERGMAN, A., KLASSON WEHLER, E., NILSSON, A. and KUROKI, H., 1995, Synthesis and mass spectrometry of methoxylated PCBs. Chemosp here, 30, 1921–1938.
   Web of Science ®Google Scholar
• BERGMAN, A., LARSEN, G. L. and BAKKE, J. E., 1982, Biliary secretion, retention and excretion of five 14C-labelled polychlorinated biphenyls in the rat. Chemosphere, 11, 249–253.
   Web of Science ®Google Scholar
• BERGMAN, A., NILSSON, A., RIEGO, J. and Om, U., 1990, Synthesis of 14C-labelled and unlabelled coplanar polychlorinated biphenyls (PCBs). Acta Chemica Scandinavica, 44, 1071–1076.
   Google Scholar
• BHAT, H. K. and ANSARI, G. A., 1990, Cholesterol ester hydrolase mediated conjugation of haloethanols with fatty acids. Chemical Research in Toxicology, 3, 311–317.
   PubMed Web of Science ®Google Scholar
• BUCMA, R., MAKITA, Z., KOSCHINSKY, T., GERAMI, A. and VLASSARA, H., 1993, Lipid advanced glycosylation: pathway for lipid oxidation in vivo. Proceedings of the National Academy of Sciences, 90, 6434–6438.
   PubMedGoogle Scholar
• CHADWICK, R. W., GEORGE, S. E. and CLAXTON, L. D., 1992, Role of the gastrointestinal mucosa and microflora in the bioactivation of the dietary and environmental mutagens or carcinogens. Drug Metabolism Reviews, 24, 425–492.
   PubMed Web of Science ®Google Scholar
• CHRISTIE, W. W., 1989, The preparation of derivates of fatty acids. In W. W. Christie (ed.), Gas Chromatography and Lipids (Ayr: Oily Press), pp. 65–66.
   Google Scholar
• DAWSON, R. M. C., 1984, Products of degradation of phospholipids. In G. Zweig, J. Sherma and H. K. Mangold (eds), Handbook of Chromatography, Lipids (Boca Raton: CRC Press), pp. 545–554.
   Google Scholar
• DODDS, P. F., 1995, Xenobiotic lipids: the inclusion of xenobiotic compounds in pathways of lipid biosynthesis. Progress in Lipid Research, 34, 219–247.
   PubMed Web of Science ®Google Scholar
• EVSTIGNEEVA, R., 1993, Chemical stability. In G. Ceve (ed.), Phospholipids Handbook (New York: Marcel Dekker), pp. 323–333.
   Google Scholar
• FEARS, R., 1985, Lipophilic xenobiotic conjugates: the pharmacological and toxicological consequences of the participation of drugs and other foreign compounds as substrates in lipid biosynthesis. Progress in Lipid Research, 24, 177–195.
   PubMed Web of Science ®Google Scholar
• FIESER, L. F. and FIESER, M., 1967, Reagents for Organic Synthesis, vol. 1 (New York: Wiley), pp. 191–192.
   Google Scholar
• GOLDMAN, P., 1989, Germ free rats in the study of the metabolites of xenobiotics compounds. In D. H. Hutson, J. Caldwell and G. D. Paulsen (eds), Intermediary Xenobiotic Metabolism in Animals: Methodology, Mechanism and Significance (London: Taylor & Francis), pp. 263-276.
   Google Scholar
• GUICHARDANT, M., TAIBE-TRONCHE, P., FAY, L. B. and LAGARDE, M., 1998, Covalent modification of aminophospholipids by 4-hydroxynonenal. Free Radicals in Biology and Medicine, 25, 1049–1056.
   Google Scholar
• HAYDEN, P., WELSH, J., YANG, Y., SCHAEFER, W., WARD, A. and STEVENS, J., 1992, Formation of mitochondrial phospholipid adducts by nephrotoxic cystein conjugate metabolites. Chemical Research in Toxicology, 5, 231–237.
   Web of Science ®Google Scholar
• HAZEN, S. L., HELLER, J., Hsu, F.-F., D'AviuNoN, A. and HEINECKE, J. W., 1999, Synthesis, isolation and characterization of the adduct formed in the reaction of p-hydroxyphenylacetaldehyde with the amino headgroup of phosphatidylethanolamine and phosphatidylserine. Chemical Research in Toxicology, 12, 19–27.
   Google Scholar
• HUTSON, D. H., 1982, Formation of lipophilic conjugates of pesticides and other xenobiotic compounds. In D. H. Hutson and T. R. Roberts (eds), Progress in Pesticide Biochemistry, vol. 2 (Chichester: Wiley), pp. 171–184.
   Google Scholar
• JERINA, D. M. and DALY, J. W., 1974, Arene oxides: a new aspect of drug metabolism. Science, 185, 573–581.
   PubMed Web of Science ®Google Scholar
• KAPHALIA, B. S. and ANSARI, G. A., 1989, Hepatic fatty acid conjugation of 2-chloroethanol and 2-bromoethanol in rats. Journal of Biochemical Toxicology, 4, 183–188.
   PubMedGoogle Scholar
• KLASSON WEHLER, E., BERGMAN, A., BRANDT, I., DARNERUD, P. O. and WACHTMEISTER, C. A., 1989, 3,3',4,4'-Tetrachlorobiphenyl: excretion and tissue retention of hydroxylated metabolites in the mouse. Drug Metabolism and Disposition, 17, 441–448.
   PubMedGoogle Scholar
• KLASSON WEHLER, E., HOVANDER, L. and LUND, B.-0., 1996, 2,2, 4,5,5 '-Pentachlorobiphenyl: comparative metabolism in the mink (Mustela vison) and the mouse. Chemical Research in Toxicology, 9, 1340–1349.
   Google Scholar
• KLASSON WEHLER, E., KOWALSKI, B., BERGMAN, A. and BRANDT, I., 1987, Metabolism of 2,3,4%6-tetrachlorobiphenyl: formation and tissue localization of mercapturic acid pathway metabolites in mice. Xenobiotica, 17, 477–486.
   PubMedGoogle Scholar
• KLASSON WEHLER, E., LINDBERG, L., BRANDT, I., JöNssoN, C. J. and BERGMAN A., 1993, Tissue retention and metabolism of 2,3,3',4,4'-pentachlorobiphenyl in mink and mouse. Chemosp here, 27, 2397–2412.
   Google Scholar
• KOU,a, N., BEPPU, M. and YOSHIMURA, H., 1990, Metabolism in vivo of 3,4,5,3',4'-pentachlorobiphenyl and toxicological assessment of the metabolite in rats. Journal of Pharmaco-Biological Dynamics, 13, 499–506.
   Google Scholar
• LARSEN, G., 1988, Deconjugation of biliary metabolites by microfloral-glucuroniases, sulphatases and cysteine conjugate [3-lyases and their subsequent enterohepatic circulation. In I. Rowland (ed.), Role of the Gut Flora in Toxicity and Cancer (London: Academic Press), pp. 79–107.
   Google Scholar
• LARSEN, G. and BAKKE, J. E., 1981, Enterohepatic circulation in formation of propachlor (2-chloro-l-isopropylacetanilide) metabolites in the rat. Xenobiotica, 11, 423–480.
   Google Scholar
• LEIGIURV, E. and FENTIMAN, A., Jr, 1981, In vitro conjugation of the trichloroethylene metabolite trichloroethanol to a fatty acid. Research Communications in Chemical Pathology and Pharmacology, 32, 569–572.
   Google Scholar
• LEIGIRRV, E., FENTIMAN, A. and FOLTZ, R., 1976, Long-retained metabolites of A9- and A8-tetrahydrocannabinols identified as novel fatty acid conjugates. Research Communications in Chemical Pathology and Pharmacology, 14, 13–28.
   PubMedGoogle Scholar
• LEIGIRRV, E., FENTIMAN, A., Jr AND THOMPSON, R., 1980, Conjugation of fatty acids to DDT in the rat: possible mechanism for retention. Toxicology, 15, 77–82.
   PubMedGoogle Scholar
• LIN, P.-H., SANGAIAH, R., RANASINGHE, A., UPTON, P. B., LA, D. K., GOLD, A. and SWENBERG, J. A., 2000, Formation of quinonoid- derived protein adducts in the liver and brain of Sprague—Dawley rats treated with 2,2',5,51-tetrachlorobiphenyl. Chemical Research in Toxicology, 13, 71 O.718.
   Google Scholar
• NOASTAOM, R. J., SIMON, M. and MuLyntiLL, M. J., 1986, A gel permeation/column chromatography cleanup method for the determination of CDDs in animal tissue. International Journal of Environmental and Analytical Chemistry, 23, 267–287.
   Google Scholar
• ELITN, U. and KLASSON WEHLER, E., 1998, Metabolism of 2,2',4,4'-tetrabrominated diphenyl ether in rat and mouse. Xenobiotica, 28, 199–211.
   PubMedGoogle Scholar
• RADWAN, S. S., 1984, Glycerophospholipids. In H. K. Mangold, G. Zweig and J. Sherma (ed.), Handbook of Chromatography, vol. 1: Lipids (Boca Raton: CRC Press), pp. 486–487.
   Google Scholar
• SAFE, S., 1984, Polychlorinated biphenyls (PCBs) and polybrominated biphenyls (PBBs): biochemistry, toxicology, and mechanism of action. CRC Critical Reviews in Toxicology, 13, 319–395.
   Google Scholar
• STEINWANDTER, H., 1982, Contributions to the application of gel permeation chromatography in residue analysis. 1. Gel-chromatographic separation of chlorinated pesticides and polychlorinated biphenyls (PCBs) in the binary solvent system dichloromethane-cyclohexane. Fresenius Z. Analytical Chemistry, 313, 536–538.
   Google Scholar
• SUNDSTR6M, G., 1973, Polychlorinated biphenyls II. Synthesis of some tetra- and pentachlorobiphe-nyls. Acta Chemica Scandinavica, 27, 600–604.
   Google Scholar
• TRELOAR, T., MADDEN, L. J., WINTER, J. S., SMITH, J. L. and DE JERSEY, J., 1996, Fatty acid ethyl ester synthesis by human liver microsomes. Biochimica et Biophyska Acta, 19, 160–166.
   Google Scholar
• TREXLER, P. and REYNOLDS, L., 1957, Flexible film apparatus for rearing and use of germ free animals. Applied Microbiology, 5, 406–442.
   PubMedGoogle Scholar
• TUNEK, A., SJODIN, K. and 1-1ALLsTaOm, G., 1997, Reversible formation of fatty acid esters of Budesonide, an antiasthma glucocorticoid, in human lung and liver microsomes. Drug Metabolism and Disposition, 25, 1311–1317.
   Google Scholar
• YISAK, W., AGURELL, S., LINDGREN, J.E. and WIDMAN, M., 1987, In vivo metabolites of cannabinol identified as fatty acid conjugates. Journal of Pharmaceutics and Pharmacology, 30, 462–463.
   Google Scholar
• YOSHIMURA, H., YONEMOTO, Y., YAMADA, H., KOGA N., OGURI, K. and SAEKI, S., 1987, Metabolism in vivo of 3,3',4,4'-tetrachlorobiphenyl and toxicological assessment of the metabolites in rats. Xenobiotica, 17, 897–910.
   Google Scholar